


Roxy: Teach John how to Fuck a Woman™

by Classpectanon (TTMIYH)



Series: Classpectanon's Miniature Smutfics [3]
Category: Homestuck
Genre: Awkward First Times, Awkwardness, Best ship, F/M, First Time, The many tags listed under the phrase "Awkward"
Language: English
Status: Completed
Published: 2016-07-06
Updated: 2016-07-06
Packaged: 2018-07-22 00:35:49
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,122
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7411430
Author URL: https://archiveofourown.org/users/TTMIYH/pseuds/Classpectanon
Summary: <blockquote class="userstuff">
              <p><span class="roxy">"No, come- come back here, you beautiful disaster, you~"</span> Roxy shouted, grabbing the blue-pyjama'd Heir of Breath by the windsock and tugging him back onto the bed with her monstrous and pretty much unexplained bonkers strength. She, however, had already stripped out of her Rogue shirt and mask, and sat there with her adorable palmfuls out on full display.</p>
<p>In this world outside of time, where the sky was literally colorless and time and space had pretty much no meaning, John and Roxy had decided to take a couple hours of rest before they brought the Land of Wind and Shade back to the new old new session (?). So... With a tiny bit of alcohol and a lot of moxie, Roxy had convinced him that he should lose his virginity, since things were going to get mad chaotic by the time they got back. And, of course, who to lose it to but to her? Roxy smirked at the thought.</p>
<p>Unfortunately, John was literally clueless.</p>
<p>Worse than Jake <span class="jake">"Oh, That's Nice, Miss Crocker!"</span> English.</p>
            </blockquote>





	Roxy: Teach John how to Fuck a Woman™

"No, come- come back here, you beautiful disaster, you~" Roxy shouted, grabbing the blue-pyjama'd Heir of Breath by the windsock and tugging him back onto the bed with her monstrous and pretty much unexplained bonkers strength. She, however, had already stripped out of her Rogue shirt and mask, and sat there with her adorable palmfuls out on full display.

In this world outside of time, where the sky was literally colorless and time and space had pretty much no meaning, John and Roxy had decided to take a couple hours of rest before they brought the Land of Wind and Shade back to the new old new session (?). So... With a tiny bit of alcohol and a lot of moxie, Roxy had convinced him that he should lose his virginity, since things were going to get mad chaotic by the time they got back. And, of course, who to lose it to but to her? Roxy smirked at the thought.

Unfortunately, John was literally clueless.

Worse than Jake "Oh, That's Nice, Miss Crocker!" English.

When she guided his hands to her breasts, he gulped and yelped like he was desecrating a forbidden idol. "D-Dad said I should never touch a lady there w-without her permission..."

"Well, Johnny boy, this is my permission." She had responded, with a hefty wonk, and clamped his wrists down onto her shirt.

That was five minutes ago, and now that her shirt was off outright, John was running for the hills. Roxy kept him there with a lazy grip. "Look, John, either you're gonna have to take your shirt off to escape my mighty grasp, or you can just get your cute tush back here and keep yer decency for a smudge." Roxy said, not waiting for him to make a decision, instead, yanking him back by the hood. John yelped as she bear-hugged him into her chest.

"Now, you know what these are, right?" Roxy said. She had to make sure she had the basics covered.

"Buh-buh-buhbb..." John stammered, his lips melting.

"Breasts. Boobs. Titties. Ta-tas. Rumble spheres. Get the picture?" Roxy responded, clamping his wrists down onto her nude top. "And those thingies in the middle, the little - ah - careful... the... the pink ones."

"N-Nh..."

"Close enough."

Roxy sat there for about a minute while John's hands (so strong~!) gently kneaded her breasts like bread dough. It was clear that he had zero idea what he was doing. When she was confident he wouldn't try to run away (she could tell because his entire body was red like a tomato), she let go of his wrists, like a dad letting go of the bike and the kid convinced they were still holding on and bammo, now John Egbert was a Professional Fondler™ (not really). Roxy was starting to breathe a bit heavily - if nothing else, he was a fast learner.

"C-Careful with the nip-nops... You're pinchin' em~" Roxy said, not sure if she was trying to make him keep doing that or stop. When he kept doing it, she made up her mind, like Schrodinger's Foreplay.

Slowly, she sneaked his hood into her hand, and then disappeared her pants off of herself, immediately spreading her legs. John gulped and squealed like a pig being stepped on. He immediately tried to run away, so Roxy tugged on the hood and he went in a circle, hovering in the air and looping back over himself and landing right back in her lap, so he dispersed into wind and flew away.

Roxy sat there for a couple of minutes in shocked silence, holding an empty pile of clothing, and started to wail. Part of it was a calculated maneuver, to get chivalrous Mr. Egbert to return to his bedroom, and part of it was because she really did feel dejected. Did she come on too strong? Did John not like her that way? Was she... Raping him? Or at the very least, not doing this right?

It was only when John, now nude, returned with a condom and lube, several minutes later, did she cheer up. And when he fumbled for another couple of minutes, trying to first figure out how to rip the condom package open without accidentally tearing it in half (he went through two this way), and then trying to get rid of the air bubble, and then finally putting it on and applying ample amount of lube. It was kind of gross, but, at least he knew how to have safe sex (thanks, Dirk, for the... in depth archives).

He then immediately jumped onto her and started to poke at her urethra. It was all Roxy could do to not laugh right in his face, big globs of spittle spraying from her plump lips, and instead, she just stifled a large exhale.

"John. John. Jhon. Johen. JOhnny. You're... Wrong hole." She said, reaching down to grab the base of his length and pull it downward so that it was at the right spot.

In one swift curve, he pushed into her, and Roxy gasped. He... was horrible. John had zero technique, zero positioning knowledge, and was trying to curl into an armadillo, his head sandwiched between her breasts while he clutched her like a teddy bear, but he filled her up nice and he could out-stamina a horse. Roxy was mostly silent, occasionally squeaking when he thrust particularly hard, while John constantly murmured questions and phrases.

"Does it hurt?"

"Nop!" Roxy whispered back, as she felt a tiny trickle of blood run down her pelvis. Ah, yes. The hymen. Curse biology.

"Does it feel good...?"

"Mmhmm..." Roxy said, kissing at his neck - he wasn't as great as some of the best times with her toys, but as a first for human intimacy, he did admirably well.

"Do you need me to move?"

"Just... Here, lemme..."

"A-Ah... Roxy, my arm-"

"Oh, oh my gosh, are you okay?"

"No, my arm just fell asleep!"

"...You stopped for /that/?"

John looked rather dejected, shaking out his tingly arm.

"You are the most adorable person in this universe or any otha~!" Roxy chirped, grabbing the sides of his face and kissing him all over. "Don't worry about it! I was joking!" She was trying really hard to make sure he didn't look down. She pulled his face into her shoulder and clung like a koala bear as he started up again.

"Still feel good?"

"Wait... Can you move your hips up... Yeaaaahh, that's the spot~!"

"Okay-"

"NffffUCK you're big!"

"Th-thanks?"

"What're you slowin' down for, hon? Mind going a lil-AIIIIEE!"

"Too fast?"

"No, nononono! Can you do that again, but, for, like, ten minutes?"

"Alright, um, give me a sec, and..."

And then they boned. It was glorious.


End file.
